Chastity Tranny Stories

8,131 results
Orientation
Length
Source
Infinite Scroll

Erin & Jeremy Ch. 03

by JDay on Sep 16, 2017
Novels and Novellas

Erin & Jeremy Chapter 3: And She Thought The Ride Was Over . . . Author’s Note: I would again like to thank agirl2envy for her help in this project. The name has remained changed to protect the sexy one. Erin sped up as she pulled on to the nearly deserted road. As she drove, the events of the last few days replayed themselves for her: Meeting her cyber-l...

Letter from Gander Cove

by justincbenedict on Nov 20, 2018
BDSM

Dear Shoeblossom, My teachers always said to me, "Norbert, you'll never amount to much, smoking weed and playing video games..." but I found I had hidden talents... Recently I joined a sadomasochistic group. It's a local thing. Amazingly, I met the hottest girl who wanted me to punish her! Victorine is a very attractive woman who's got about twelve or thi...

A One Night Stand for Tranny G

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

The time had arrived for me to travel to see Tranny G, yet something felt different. I mentioned that HE is a soldier and really, I was never angry about the rape. It was such an experience, that I wander back to and repeat in my mind again and again, wet with the memories of the fear, the fight, the ultimate pleasure. I might as well tell you that I see mys...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Indolent Ivan

by justincbenedict on Aug 27, 2018
BDSM

February 24 From JosephineMiller To: Wrenjohnson Wren, this is great. I couldn't believe it. Ivan proposed last night. He presented me with a diamond engagement ring. I was kind of like "I hope this isn't a bribe, you're still not getting to orgasm till the end of next month." Although for a ring like that, I might have given up the whole Mistress/Slave t...

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Writing Erotica For The First Time

by LitKate on Sep 16, 2017
Transsexuals & Crossdressers

I always found it somehow difficult to type on a laptop when it was actually on my lap. Even more difficult when crammed into a car that's driving around on bumpy af roads. But I had wanted to try writing erotica. Nothing overly fetishy or magical. Just something that spoke to what it's actually like being like a modern trans girl or whatever. I just wished...

The Evolution of Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

My beloved Tranny G was so devastated by the one night stand and had lost her confidence. First she was made fun of while shopping, ending the evening with the "perfect" man, having her first true intimate experience with a man, only to find that his promise to call her was false. I did not see her on my last trip, as she was devastated and in her own lovi...

Tranny G is a Nymph

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

It has been a long winter and I have not seen Chris or Tranny G in a long time. Chris lives in a place too cold and it is difficult for him to travel. During those cold months, and without my being near, G has been in hiding. I have hinted, begged and pleaded with Chris to find a weekend to travel to see me. He needs a break from work and the cold and I need...

Tranny G, Gang Bang Queen, 5

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I apologize - I had no idea I would continue to write about Chris and Tranny G or I would have numbered the stories. These two beloved people are so rooted in my life and there is so much to share. I never imagined I would share these stories with anyone. Since my husband and I became swingers, I had no idea what my interests would be, I just simply plunged...